Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-Oximes
The enantioselective 5-<i>exo</i>-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolu...
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| Format: | Article |
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MDPI AG
2019-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/19/3464 |
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| author | Taiki Rouno Tomoki Niwa Kousuke Nishibashi Nobuharu Yamamoto Hiromichi Egami Yoshitaka Hamashima |
| author_facet | Taiki Rouno Tomoki Niwa Kousuke Nishibashi Nobuharu Yamamoto Hiromichi Egami Yoshitaka Hamashima |
| author_sort | Taiki Rouno |
| collection | DOAJ |
| description | The enantioselective 5-<i>exo</i>-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry of the major isomer was determined to be <i>S</i> by comparison with the literature after transformation of the product to the corresponding iodinated isoxazoline. |
| first_indexed | 2024-12-11T20:01:17Z |
| format | Article |
| id | doaj.art-a6f5804be0a5404dadc3c8022a79da6e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T20:01:17Z |
| publishDate | 2019-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a6f5804be0a5404dadc3c8022a79da6e2022-12-22T00:52:30ZengMDPI AGMolecules1420-30492019-09-012419346410.3390/molecules24193464molecules24193464Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-OximesTaiki Rouno0Tomoki Niwa1Kousuke Nishibashi2Nobuharu Yamamoto3Hiromichi Egami4Yoshitaka Hamashima5School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanThe enantioselective 5-<i>exo</i>-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry of the major isomer was determined to be <i>S</i> by comparison with the literature after transformation of the product to the corresponding iodinated isoxazoline.https://www.mdpi.com/1420-3049/24/19/3464fluorineasymmetric catalysisphase-transfer catalysisoxime |
| spellingShingle | Taiki Rouno Tomoki Niwa Kousuke Nishibashi Nobuharu Yamamoto Hiromichi Egami Yoshitaka Hamashima Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-Oximes Molecules fluorine asymmetric catalysis phase-transfer catalysis oxime |
| title | Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-Oximes |
| title_full | Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-Oximes |
| title_fullStr | Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-Oximes |
| title_full_unstemmed | Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-Oximes |
| title_short | Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-Oximes |
| title_sort | enantioselective 5 i exo i fluorocyclization of ene oximes |
| topic | fluorine asymmetric catalysis phase-transfer catalysis oxime |
| url | https://www.mdpi.com/1420-3049/24/19/3464 |
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